macos Sequoia causing problems with messages on mac

After updating my iPhone 15 pro max to ios 18 and my 2019 iMac to Sequoia messages no longer updates on my iMac. I can still read what was there before the updates but not afterwards. I also cannot send messages from my iMac. Messages is still working on iPhone.

iMac (2017 – 2020)

Posted on Sep 17, 2024 11:55 AM

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Posted on Oct 21, 2024 11:36 PM

NotSoTechnical wrote:

Yup, I run OpenVPN 24/7, and have been having problems sending messages since upgrading to Sequoia. Turning off my VPN allows the messages to go.

I rarely experience bugs with Apple software, but this one is a major foo bar! Let's see a fix, Apple!

And in your mind it’s impossible that it is a problem with OpenVPN? Really? Have you considered this:


When you install VPN it configures itself to the specific hardware, OS version and network that the device uses. If any of those change it can break the VPN. So any time you change any of these you may need to delete the VPN app and profile, restart your iPhone, iPad or Mac then add them back (if you still want to use VPN) so it can configure itself to the new environment.





177 replies

Oct 11, 2024 6:36 PM in response to erichschienke

erichschienke wrote:
Anyhow, it's b.s. and Apple shouldn't be allowed to pick the winners and losers in the VPN market... they call that a monopoly.

Apple doesn’t pick any apps. Anyone who creates an app that meets Apple’s security standards can list it in the App Store. And if it isn’t in the app store its risky.


I’m not sure why you are using VPN, but if it’s because you think it is more secure than not using VPN you are wrong.


The provider of the VPN knows everything about you and your location, as well as what sites you access through the VPN. So you are totally dependent on the VPN provider’s honesty. As a start, if the VPN is free, DON’T USE IT. The provider has to make money somehow, and if you aren’t paying them then they are selling your private data to make money. And it was recently discovered that a major wholesaler of "free" VPN that is provided by many "free" VPN deliverers also makes your computer a node in a worldwide botnet used to hack other users.


But even those that charge can’t necessarily be trusted. For example, a few years ago Avast was caught selling user browsing data. They claim they have stopped doing so, however, they lied 🤥→ FTC Order Will Ban Avast from Selling Browsing Data for Advertising Purposes


You don’t really need VPN when using public Wi-Fi, because all communications between your device and the servers it accesses are end-to-end encrypted.


If you want VPN for privacy about the sites you visit, that’s not a good choice as discussed; instead you should download and use the TOR browser.


The other use for VPN is to “steal” content that is not available in your area. I leave this question to your personal ethics.


With iOS 15.2 and later for iOS/iPadOS and MacOS Monterey 12.2 and later Apple now has iCloud+ Private Relay, which is not VPN, but provides a safer browsing environment than VPN, and it doesn't spy on you→About iCloud Private Relay - Apple Support



Oct 11, 2024 8:14 PM in response to Lawrence Finch

Thanks chucklehead.


For those of us who have ISPs that throttle bandwidth based on packet shaping and sniffing, which they continue to do, I prefer to have all my traffic going through a secure tunnel. Get real, this whole thread wouldn't exist without A LOT of Apple users connecting via VPNs. If you connect to any sort of Federal server, you need to do it via some sort of VPN. Also, connecting in China and other out-of-the-way places, having to use a VPN just to access gmail, it becomes the only way to get online.


[Edited by Moderator]

Oct 15, 2024 8:53 AM in response to Ignatz Ratzkiwatzki

Apple Services is essentially everything iCloud-related: Messages, iCloud email, Podcasts, the Stock App, Weather App, the App Store, Calendar, Address Book, FaceTime, etc.


As for running your browser as root, if you're asking, then you're not doing that and you're all good :-) Using the terminal (command line), you can launch browsers and other apps as the super-user for certain purposes, but it's a very deliberate thing. That's something you need to be concerned about.


The most significant risk to you is not browsers as root, but a hostile network like a hotspot someone set up at Starbucks. Malicious people can route other traffic that's non-Apple using this "hole" in your VPN. Before anyone jumps on me saying "that never happens," I am in a business where I see this every day in certain populated areas, airports, and cafés. So it is something you need to be concerned about if you frequently pop onto hotspots in public places.

Oct 16, 2024 6:52 PM in response to Ignatz Ratzkiwatzki

Apple HAS fixed their OS. VPN is a major tool of hackers. Financial institutions frequently block connections over VPN. If you connect to SnapChat over VPN you will be banned, and if you do it consistently you can be banned for life. Facebook will block some VPN connections. By blocking VPN for messages Apple is protecting users.

Oct 16, 2024 7:41 PM in response to fherr

@Lawrence Finch The suggestion that Apple has “fixed its OS” is not consistent with the fact they have apparently solved this problem in upcoming versions.

The idea that by blocking VPNs Apple is “protecting users” will be news to people in China and other oppressive regimes.

Facebook and other data hoarders blocked VPNs because they want to collect and sell our information. 

Thank you for letting us know about SnapChat’s policy. I’ve never their “service” but would be proud to be banned from their site for life. 

Oct 17, 2024 3:14 AM in response to Lawrence Finch

@lawrence finch


Lies. Every other service, server and website I use is working as it should with VPN on! Even iMessages on my iPhone is working with VPN on. The only issue I’m having is with iMessage on OS 15. Apple is punishing its loyal and faithful customers who are simply trying to protect their online anonymity. If you don’t have anything logical to add to the conversation, I’d suggest staying out of it.  Can someone explain to me why iMessage works fine on iOS with VPN on but not on OS?

Oct 17, 2024 3:53 AM in response to TankvilleFarmer

Lies indeed. I believe I can try and simplify a bit. On macOS, apps make changes to routing, and monitor status in ways not possible using macOS's VPN Service. That is why you still have an app even when the app does use the macOS VPN Service API.


But on iOS, apps cannot control the network in the same sophisticated ways. Connections can persist across a VPN going down, DNS will leak if it's already cached, etc. This is a limitation of iOS that is not there in macOS. The only thing you can really do on the phones is toggle airplane mode (assuming you're using Wi-Fi and LTE) while connected to the VPN. This will effectively close any open connections, and then restart them through the VPN.


And re My Finch, Lawrence you seem not to use a VPN and have interesting and strong opinions against them, but since you don't have any knowledge that's germane here, I respectfully ask you leave the group alone while we try and resolve this and stay informed together.

Oct 17, 2024 7:26 AM in response to Cthulhu

Cthulhu wrote:

And re My Finch, Lawrence you seem not to use a VPN and have interesting and strong opinions against them, but since you don't have any knowledge that's germane here, I respectfully ask you leave the group alone while we try and resolve this and stay informed together.

No, I no longer use VPN, except to access my office network through its firewall, which works perfectly all the time.


Here is one reason I don't→Don't use VPN - GITHUB

Here is another: Brian Krebs on VPN security (or lack thereof)→Why your VPN may not be as secure as it claims


And most of all, because I use iCloud+ Private Relay, which is not VPN, but provides a safer browsing environment than VPN, and it doesn't spy on you→About iCloud Private Relay - Apple Support



Oct 17, 2024 8:03 AM in response to Lawrence Finch

Lawrence, I am begging you here buddy, please just unsubscribe from this topic. VPNs are not proxies, Apple's Private Relay does nothing but hide your IP (and only for a fraction of your traffic) and your browser's fingerprint still identifies you; and the second article is just an esoteric thing to happen under specific circumstances and is a but like saying "don't ever go outside ever, or else a bird can poop on you."


Some of us use VPNs for work so that we CAN be tracked because we're required to do so. And if you access your office through a "Firewall" you're missing all the authentication you need to secure that traffic, and opening yourself up to all the ssh and Boring/Open/LibreSSL and other bugs out there.


PLEASE! All thousand of us here get that you don't like VPNs, but you are making wild assumptions about why we use them and how. No one claimed they are a magical network security panacea. Respectfully, please, add to the solution or unsubscribe.

Oct 17, 2024 9:21 AM in response to fherr

When did this thread become a pros and cons of using a VPN? Mr. Finch, you seem very knowledgeable on the subject of VPN's. However the title of the article you reference is "Why your vpn MAY not be as secure as you think". I doubt the majority of Apple Community participants would be able to understand 97% of the article. Plus, if you read the thread below the article you'll find a number of people who are not as skeptical as you and the articles writers are.

Oct 17, 2024 2:19 PM in response to Lawrence Finch

Lawrence Finch wrote:

Apple HAS fixed their OS. VPN is a major tool of hackers. Financial institutions frequently block connections over VPN. If you connect to SnapChat over VPN you will be banned, and if you do it consistently you can be banned for life. Facebook will block some VPN connections. By blocking VPN for messages Apple is protecting users.

I'm sorry but this just isn't true. This is 100% a bug in MacOS, and is only affecting Apple-related traffic. By no means is this intentional on Apple's part to discourage users from using VPNs. That's just silly.


Let's try to keep comments on the topic of this bug, and not personal opinions about VPNs.

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macos Sequoia causing problems with messages on mac

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